Roger never accepted his conviction for kidnapping John Factor.
After seven years in prison, he became a jail- house lawyer, pouring over his court transcripts, and as a result became something of an expert in the writ of habeas corpus.5 He wrote his own appeals to the governor but after a while they were returned unopened.
Of his frustration Touhy wrote, “denied without a hearing...denied without a hearing... denied without a hearing....How could I get justice if no court would listen to me? I was nailed in a box and I had no hammer to batter my way out.”
Then, in the latter part of August, 1942, Touhy decided to escape from prison for a somewhat peculiar reason.
“I stayed awake until dawn in my cell, thinking. I was without hope. I was buried alive in prison and I would die there. I couldn't see a light ahead anywhere. Nothing but darkness and loneliness and desperation. The world had forgotten me after eight years. I was a nothing. Well, there was one way I could focus public attention on my misery. I could escape. I would be caught of course but the break would show my terrible situation. What cockeyed thinking that was....my mental attitude was a mess, I later came to realize”.
The inmate who came to him with the idea of escaping was Gene O'Connor, who had probably known Roger on the outside, since O'Connor had been the business agent of the Chicago Awning and Tent Makers Union-or at least he was until he was arrested for intimidation after firing a shot at a union member who opposed him in a race.
Now, O'Connor was serving a life sentence for a May 1932 robbery in which a Chicago policeman had been gunned down in cold blood.
Escaping for O'Connor was a way of life. In 1936 he escaped from Statesville after he found his way into the central electric room, pulled the main power switch and then scaled the walls to freedom. He was captured and escaped again a year later only to be caught within a week.
The time seemed ripe again for escape. The war had taken away the younger guards, leaving mostly older men, some coming out of retirement to resume duty. Since they were paid starvation wages, O'Connor had primed the escape by bribing the tower guards with items lifted from prison kitchen storehouses where Touhy worked. These foods were almost impossible to get during wartime rationing: 100 pound sacks of sugar, bags of coffee, slabs of bacon and quarter sides of beef all of which could be resold on the outside for big money. Adding to the plan's credibility was the fact that E.H. Stubenfield, an old time political hack, was now warden. He had replaced the far better qualified Joseph Ragen, who had resigned in protest against political meddling inside the prison. As a result, the prison's once tight security had gone lax.
The keys to the escape were guns. Two pistols were left at the base of the prison's flagpole by the brother of another inmate, Eddie Darlak, who was in on the break. A trustee had brought two guns into the prison, carried inside wrapped in the American flag which he lowered each evening outside the prison walls.
On October 9, 1942, Roger stood at the prison bakery door with an enormous pair of scissors stolen from the tailor shop, hidden inside of his blue prison-issue shirt. Several minutes later, driver Jack Cito, a convict with mob connections,6 pulled the prison laundry truck up to the door and Roger leaped up onto the driver's door and yanked Cito out on to the ground and screamed for the keys. When Cito moved too slowly, Touhy cut him with the scissors, yelling "Give me the Goddamn keys!"
Cito told Touhy the keys were in the ignition and Roger leaped into the truck and drove to the mechanic shop where the other escapees, O'Connor, Mclnerney, Darlak, Stewart and Nelson were waiting.
Touhy leaped out of the truck and O'Connor handed him a .45 caliber automatic. He rushed into the mechanic shop where he was confronted by a guard, Lieutenant Samuel Johnston, who asked Touhy "Why are you here, what are you doing here?"
Roger didn't answer but began snapping the prison telephone wires with his long scissors. As Johnston was about to club Touhy into submission, Basil Banghart came through the window with a pistol at ready and ordered Johnston to unlock a set of ladders. At that same moment, guard George Cotter arrived on the scene and was overpowered and beaten to the floor.
Placing the guards' white hats on their heads, they pushed Cotter and Johnston outside and forced them to load the ladders on to the back of the truck and ordered them to sit on the ladders to keep them from falling off. Then Roger shouted, "Ok, go, go go!" at Stewart, who was behind the wheel, but the truck stalled.
Touhy leaped off the back of the vehicle, pulled Stewart out of the driver's seat and tried to get the truck started but couldn't. Deciding to jump start the truck, Roger looked over to the 300 inmates crowding around to watch the excitement. Roger yelled for the convicts to push the truck, which they did. The motor turned over with a roar.
They sped across the yard, driving to Tower Three in the northwest corner. At the base of the tower they forced guard Johnston to help them put the ladders together. When he refused, they beat him, tore his shirt off and took him up the ladder with them. Roger looked up into the tower and could see one of the guards who they had bribed7 standing to one side of the tower, at the end of the walkway. "He wasn't holding a gun but he didn't have far to reach for one, " Touhy said.
Roger fired a single shot which blew out the guardhouse window, striking the guard in the forehead with flying glass and knocking him to the floor. When they were all inside the tower, Darlak took the guard's car keys. Though it was against prison regulations, the car was parked at the base of the prison wall, just feet away from the tower.
Before leaving, the convicts took two high-powered prison-issue rifles, a pistol and 115 to 120 rounds for each gun. They then walked calmly down the tower stairs, into Krause's car, and roared away toward Chicago.